Synthesis of Dihydroindoloisoquinolines through Copper‐Catalyzed Cross‐Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes

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Title: Synthesis of Dihydroindoloisoquinolines through Copper‐Catalyzed Cross‐Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes
Authors: Martín-García, Iris | Alonso, Francisco
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: C−C coupling | Copper nanoparticles | Heterogeneous catalysis | Nitro compounds | Nitrogen heterocycles
Knowledge Area: Química Orgánica
Issue Date: 16-Oct-2018
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Chemistry - A European Journal. 2018, 24(71): 18857-18862. doi:10.1002/chem.201805137
Abstract: Lately, the cross‐dehydrogenative coupling of tetrahydroisoquinolines and nitroalkanes has become a widely studied reaction in organic chemistry; the corresponding β‐nitroamines are generally formed irrespective of the catalysis and activation mode utilized. A quite distinct behavior was observed when the reaction was catalyzed by copper nanoparticles supported on titania, leading to the formation of 5,6‐dihydroindolo[2,1‐a]isoquinolines with high selectivity and good yields. A meticulous reaction mechanism is proposed, based on experimentation, and discussed along with a key chemical modification of these compounds. Apparently, the catalyst effectiveness resides in its nanostructured character, outperforming the activity of the commercial copper catalysts.
Sponsor: This work was generously supported by the Spanish Ministerio de Economía y Competitividad (MINECO; grant no. CTQ2017-88171-P), the Generalitat Valenciana (GV; grant no. AICO/2017/007), and the Instituto de Síntesis Orgánica (ISO). I.M.-G. thanks the Vicerrectorado de Investigación y Transferencia del Conocimiento of the Universidad de Alicante for a pre-doctoral grant (no. UAFPU2016-034).
URI: http://hdl.handle.net/10045/84489
ISSN: 0947-6539 (Print) | 1521-3765 (Online)
DOI: 10.1002/chem.201805137
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: https://doi.org/10.1002/chem.201805137
Appears in Collections:INV - MATCAT - Artículos de Revistas

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